October is National Cyber Awareness Month, and we’ll be spotlighting cybersecurity content on the blog all month long.

We hear the term “red team” liberally used these days, applied in the security space for both force-on-force scenario testing (subverting hardened facilities and assets) and in the information security space, primarily referring to “white hat” hacking to assess security posture for systems, devices, network perimeters and web applications.

A “red teamer” in the decision support or strategic space is formally trained and uses critical thinking tools and techniques to provoke analysis, stress test strategies, plans and perspectives. At the heart of this work is the modeling or reframing of the problem space from the adversaries perspective. Red teamers and Security Pros are by nature contrarians, and it is this contrarian mindset we want to capitalize on.

While cybersecurity “red teaming” as penetration testing is vital to an organization’s testing of its security and data protection posture, it has a narrow scope. However, everyone these days in this space wants to refer to his or her work as red teaming. The practice of decision support red teaming is the area that I am submitting an organization can immediately benefit from and are not currently employing. This is an area where your security team can add value by adopting the tools and techniques to facilitate red teaming. Information security professionals are diverse thinkers and often “see” across the entire enterprise. Equipping them with red team tools and techniques can enhance their value in guiding the organization to make better decisions.

Red teaming and the value of a premortem

So how do we do it? How do we immediately capitalize on our existing stance as contrarians to serve as strategic red teamers? There are a number of available tools such as the U.S.Army’s Applied Critical Thinking Handbook, and Bryce Hoffman’s Red Teaming. We start with, most importantly, is buy-in and genuine support from the top of the organization, and the admission that we will trust our decision to conduct red team analysis and we will be true to the results. There are a number of short tools to use to try this, one of the most straightforward is to have your security staff conduct a premortem on your most important security project for the upcoming year.

The basic approach of the premortem is to visualize, prospectively, about the project failing and using this to illuminate the cause(s) of the failure. This is not a risk assessment. We are not speculating on what could harm our project, we are identifying what actually caused the failure. This is pathology; we are engaged in diagnosis, not prognosis. Supplies needed are easy to acquire, you will need paper or index cards and pens/pencils and a white board or projector.

The leader (security staff facilitator) level sets with the group by reading out the summary from the business case or a summarized version of the project. The leader tells everybody that they should assume that their team, the project team, has made the decision to go forward and that the project has gone forward and has concluded. We are in the future now, a year into the future, and the project has been an utter failure. It has crashed and burned with no redeeming outcome or benefit.

Exercise: Each player (project team member) takes the paper in front of him/her and writes a brief narrative or cause of the failure. Take 5 minutes and work in silence.

The facilitator collects the paper or cards and generates a list of all the points on a whiteboard or projector. The facilitator can now work with the group to solicit further failure ideas, inspired by the list.

Engage in a game to further determine the top five causes for the failure. [A practical note here: if you conduct a premortem and determine a set of failures that are agreed universally by the group as being actual failures, you have a fundamental problem with your project. Stop it immediately and take a step back and rethink the plan.]

Red teaming is best conducted with as diverse a group as possible, and often times those who have had the least to do with the project plan formation can provide insights into points of failure. As you look to expand your tool set in the future, a master’s degree in security leadership can help engender this contrarian mindset and improve the value of security in your organization.

Joseph (Joe) Dalessandro is the program chair of the Information Security Leadership program at Brandeis University Graduate Professional Studies, and the Head of Security & Technology Audit and Audit Data Analytics, Australian Unity.